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Vacation Rentals in Kailua, Oahu, Hawaii

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$95
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
11 photos Details
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$147
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Studio, 1 Bathroom, Sleeps 3
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$240
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2 Bedrooms, 1 Bathroom, Sleeps 9
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Quaint tropical cottage walk to beach covered lanai
Sleeps 2
$95 / night
Your Island Home!
3 Bedrooms, sleeps 8
$500 - $995 / night
KAILUA DREAMS-MAKAI:  NEW, LUXURIOUS AND SPACIOUS LIVING
1 Bedroom, sleeps 3
$265 - $350 / night
Lola's Lanikai Loft
Sleeps 3
$200 / night
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$275
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
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$1,450
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4 Bedrooms, 2 Bathrooms, Sleeps 10
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$1,100
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6 Bedrooms, 5 Bathrooms, Sleeps 15
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$300
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$3,325
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
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$1,250
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
12 photos Details
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$4,375
Per Night
6 Bedrooms, 6 Bathrooms, Sleeps 12
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$195
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
19 photos Details
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$135
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
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$249
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
13 photos Details
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$399
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 12
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$775
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
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$1,950
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4 Bedrooms, 5 Bathrooms, Sleeps 7
22 photos Details
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$475
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
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$95
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1 Bedroom, 1 Bathroom, Sleeps 4
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$600
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2 Bedrooms, 1 Bathroom, Sleeps 4
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$2,700
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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$825
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5 Bedrooms, 4 Bathrooms, Sleeps 10
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$1,500
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4 Bedrooms, 11 Bathrooms, Sleeps 6
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$2,500
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6 Bedrooms, 4 Bathrooms, Sleeps 14
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$705
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
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$174
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1 Bedroom, 1 Bathroom, Sleeps 3
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$620
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 12
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$345
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
10 photos Details
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$6,000
Per Night
7 Bedrooms, 8 Bathrooms, Sleeps 14
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$250
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3 Bedrooms, 2 Bathrooms, Sleeps 6
31 photos Details
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$750
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
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$285
Per Night
7 Bedrooms, 5 Bathrooms, Sleeps 20
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26 photos Details
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$165
Per Night
Studio, 1 Bathroom, Sleeps 2
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30 photos Details
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$150
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
15 photos Details
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$395
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 7
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16 photos Details
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From
$3,950
Per Night
8 Bedrooms, 8 Bathrooms, Sleeps 16
14 photos Details
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From
$189
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
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15 photos Details
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$180
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
20 photos Details
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From
$1,350
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
19 photos Details
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From
$220
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
18 photos Details
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$900
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
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Suitability

  • Wheelchair access (8)
  • Elder access (27)
  • Suitable for children (35)
  • Pet friendly (2)
  • Smoking allowed (1)

Amenities

  • Internet (82)
  • Grill (73)
  • Other outdoor space (65)
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Book Online(40)

Suitability

  • Wheelchair access (8)
  • Elder access (27)
  • Suitable for children (35)
  • Pet friendly (2)
  • Smoking allowed (1)

Amenities

  • Internet (82)
  • Grill (73)
  • Other outdoor space (65)
  • Washer/Dryer (51)
  • Parking (50)
  • View all amenities
Kailua Vacation Rentals

Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

A Kailua Vacation

Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

Family-Friendly Kailua

From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.